Watershed development is an important component of rural development and natural resource management strategies in many countries. A watershed is a special kind of common pool resource: an area defined by hydrological linkages where optimal management requires coordinated use of natural resources by all users. Management is difficult because natural resources comprising the watershed system have multiple, conflicting uses, so any given management approach will spread benefits and costs unevenly among users. To address these challenges, watershed approaches have evolved from more technocratic to a greater focus on social organization and participation. However, the latter cannot necessarily be widely replicated. In addition, participatory approaches have worked better at a small scale, but hydrological relationships cover a larger scale and some projects have faced tradeoffs in choosing between the two. Optimal approaches for future efforts are not clear, and theories from common property research do not support the idea that complex watershed management can succeed everywhere. Solutions may include simplifying watershed projects, pursuing watershed projects where conditions are favorable, and making other investments elsewhere, including building the organizational capacity that can facilitate watershed management.